Deals on vacations and trips to Winchester

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Winchester flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Hayward Inn

Hayward Inn

3 out of 5
East University
Price was $785, price is now $600 per person
$600
per person
Dec 5 - Dec 11
found 4 hours ago
Roundtrip non-stop flight included
Austin (AUS) to Eugene (EUG)
This hotel features an indoor pool and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate freebies like full breakfast and free self parking.
The Gordon Hotel

The Gordon Hotel

3.5 out of 5
Downtown Eugene
Price was $983, price is now $823 per person
$823
per person
Dec 5 - Dec 11
found 4 hours ago
Roundtrip non-stop flight included
Austin (AUS) to Eugene (EUG)
This smoke-free hotel's 2 restaurants, 3 bars/lounges, and 24-hour gym are some of the featured amenities. Traveling on business? Take advantage of the business center, free WiFi in public areas, and free airport shuttle. Valet parking, a terrace, and dry cleaning are also offered.
Valley River Inn

Valley River Inn

4 out of 5
Price was $725, price is now $624 per person
$624
per person
Dec 5 - Dec 11
found 4 hours ago
Roundtrip non-stop flight included
Austin (AUS) to Eugene (EUG)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Families will appreciate the children's pool and complimentary bicycles. Enjoy the seasonal outdoor pool and perks like free self parking and a free airport shuttle.
Downtown Inn

Downtown Inn

2 out of 5
Downtown Eugene
Price was $1,168, price is now $1,007 per person
$1,007
per person
Oct 28 - Nov 1
found 18 hours ago
Roundtrip flight included
Tri-Cities (TRI) to Eugene (EUG)
This motel doesn't skimp on freebies - guests receive free WiFi and free self parking. Staff at the 24-hour front desk can provide around-the-clock assistance.
Residence Inn Eugene Springfield

Residence Inn Eugene Springfield

3 out of 5
Cal Young
Price was $888, price is now $795 per person
$795
per person
Dec 5 - Dec 11
found 4 hours ago
Roundtrip non-stop flight included
Austin (AUS) to Eugene (EUG)
This hotel features a 24-hour gym and an outdoor tennis court. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the free full breakfast each morning.

Top Winchester hotels deals

Riverfront Inn Roseburg

Riverfront Inn Roseburg

2 out of 5
315 W Harvard Ave Roseburg OR
Free Cancellation
Reserve now, pay when you stay
$79 nightly
The price is $86 total per night
$86 total
Sep 28 - Sep 29
Total with taxes and fees
This motel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including food and water bowls. There's an outdoor pool on site, and a 24-hour front desk and a terrace are also provided.
Best Western Garden Villa Inn

Best Western Garden Villa Inn

2.5 out of 5
760 NW Garden Valley Boulevard Roseburg OR
Free Cancellation
Reserve now, pay when you stay
$98 nightly
The price is $107 total per night
$107 total
Oct 4 - Oct 5
Total with taxes and fees
A restaurant and a seasonal outdoor pool are featured at this hotel. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the hot tub and free perks like buffet breakfast and free self parking.
SureStay by Best Western Roseburg

SureStay by Best Western Roseburg

2.5 out of 5
2855 NW Edenbower Blvd Roseburg OR
Free Cancellation
Reserve now, pay when you stay
$98 nightly
The price is $107 total per night
$107 total
Oct 5 - Oct 6
Total with taxes and fees
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.
Super 8 by Wyndham Roseburg

Super 8 by Wyndham Roseburg

2.5 out of 5
3200 Nw Aviation Dr I-5 Exit # 127 Roseburg OR
Free Cancellation
Reserve now, pay when you stay
$54 nightly
The price is $59 total per night
$59 total
Oct 19 - Oct 20
Total with taxes and fees
This hotel features an indoor pool and a hot tub. Business travelers can take advantage of the free WiFi in public areas. Guests will appreciate freebies like on-the-go breakfast and free self parking.
Comfort Inn Roseburg

Comfort Inn Roseburg

2.5 out of 5
1539 NW Mullholland Drive Roseburg OR
Free Cancellation
$103 nightly
The price is $113 total per night
$113 total
Oct 18 - Oct 19
Total with taxes and fees
This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the hot tub and free perks like on-the-go breakfast and free self parking.
The Lodge at Roseburg

The Lodge at Roseburg

3 out of 5
375 Harvard Blvd Roseburg OR
Free Cancellation
Reserve now, pay when you stay
$170 nightly
The price is $186 total per night
$186 total
Oct 1 - Oct 2
Total with taxes and fees
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

How much are vacation packages to Winchester?
Starting from as low as $600, hotel and flight packages are an excellent way to stretch your travel budget. Winchester, here you come!
Where can I get the best vacation package deals for Winchester?
Snapping up the perfect package deal to Winchester is a piece of cake with Travelocity. With as many as 400 airlines and 1,000,000 properties all over the globe, you're spoiled for choice when selecting your flights and hotels.
Why should I book my Winchester vacation bundle via Travelocity?
Savings, support and a stress-free booking are just the beginning. Collect lifelong memories and enjoy a fulfilling travel experience knowing you can rely on our team of customer support experts around-the-clock. With the Travelocity Price Match Guarantee, you know you're getting the best deal available.
Can I save money on my Winchester car rental if I bundle it with hotels and flights?
You sure can with our Winchester vacation packages. With one of these, there are lots of ways to make your vacation budget go further. Bundle any two or more car, hotel, flight and tour bookings and see the savings pile up. With a rental car, all the key sights in and around Winchester are just a road trip away.
Which airport is best for Winchester?
Southwest Oregon Regional Airport (OTH), the primary terminal in Winchester, is where you'll stroll through arrivals. You'll find it 45 mi west of the center of town.
Where should I stay when visiting Winchester?
Many travelers hit the hay at the Singing Waters at N. Umpqua. It's a great base for your Winchester getaway.

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